Ethyl Acetate → HCID 19801010, compound

HRID 1646638Notes

Reaction equation

HRID 1646638 reaction equation
[O:1]1[CH:3]([CH2:4][CH:5]=[C:6]([CH3:8])[CH3:7])[C:2]1([CH:10]1[CH2:15][CH:14]([OH:16])[CH:13](OC)[CH2:12][C:11]1([CH2:20][S:21][CH3:22])[OH:19])[CH3:9].[Cl:23][CH2:24][C:25]([N:27]=[C:28]=[O:29])=[O:26].[C:30](OCC)(=[O:32])C>ClCCl>[Cl:23][CH2:24][C:25]([NH:27][C:28]([O:16][CH:14]1[CH2:13][CH2:12][C:11]([CH2:20][S:21][CH3:22])([OH:19])[CH:10]([C:2]2([CH3:9])[O:1][CH:3]2[CH2:4][CH:5]=[C:6]([CH3:7])[CH3:8])[CH:15]1[O:32][CH3:30])=[O:29])=[O:26]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 78209Chloroacetyl isocyanateHCID 19801064HCID 19801064, compound

Product 1

HCID 19801010HCID 19801010, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (15 ml) was dissolved 2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-5-methoxy-1-methylthiomethyl-1,4-cyclohexanediol (1.50 g). To the solution was added dropwise, under ice-cooling, chloroacetyl isocyanate (0.46 ml). The mixture was stirred for 20 minutes, which was diluted with ethyl acetate (60 ml) and washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous saline solution, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by means of a silica gel column chromatography (carrier 75 g, developing solvent : ethyl acetate - hexane=1:2), followed by crystallization from ether-hexane to afford 4-O-(chloroacetylcarbamoyl)-2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy-1-methylthiomethyl-1,4-cyclohexanediol (1.70 g: yield 83%) as colorless crystals, m.p. 101° to 102° C.

Workup

  1. additionTo the solution was added dropwise, under ice-
  2. temperaturecooling
  3. washwashed with a saturated aqueous solution of sodium hydrogencarbonate
  4. dry with materialby drying over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by means of a silica gel column chromatography (carrier 75 g, developing solvent : ethyl acetate - hexane=1:2)
  7. customfollowed by crystallization from ether-hexane

Sources & evidence

ORD record
ord-60eff700e1834120b73cd917cb227716
Source dataset
uspto-grants-1993_01
Patent number
US05180735

Reaction notes

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